When trying to craft a DLP policy with a regex condition/exception with the ^ metacharacter to match a specific string that occurs at the beginning of the email subject, it will not match.
DLP 16.0+
For DLP Endpoint, the email subject is not treated as a separate message component but instead maps to the email envelope(header).
Refer to Detection Messages and Message Components
As such when trying to use the ^ regex metacharacter in a DLP condition to match characters at the start of the email subject, it will not match. This is because the subject does not occur at the beginning of the header.
This does not occur for email detection using Network Prevent for Email or Network Monitor detection servers as for server detection, the email subject component maps specifically to the email subject.
Refer to Selecting components to match on
If trying to match on the beginning of the email subject line don't use the ^ regex metacharacter. Instead you could try to match on something like the following as an example if looking for the word "secure" at the start of the email subject:
(?i)(subject:\s)(secure)